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Hirshfeld surface analysis and crystal structure of N-(2-meth-oxy-phen-yl)acetamide.

ABSTRACT: The title compound, C₉H₁₁NO₂, was obtained as unexpected product from the reaction of (4-{2-benz-yloxy-5-[(E)-(3-chloro-4-methyl-phen-yl)diazen-yl]benzyl-idene}-2-phenyl-oxazol-5(4H)-one) with 2-meth-oxy-aniline in the presence of acetic acid as solvent. The amide group is not coplanar with the benzene ring, as shown by the C-N-C-O and C-N-C-C torsion angles of -2.5 (3) and 176.54 (19)°, respectively. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (53.9%), C⋯H/H⋯C (21.4%), O⋯H/H⋯O (21.4%) and N⋯H/H⋯N (1.7%) inter-actions.

SUBMITTER: Yaman M

PROVIDER: S-EPMC6658953 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfan-yl]-N-(2-meth-oxy-phen-yl)acetamide.

Project description:In the title compound, C16H14N2O3S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004?Å) and makes a dihedral angle of 66.16?(17)° with the benzene ring of the meth-oxy-phenyl group. Two intra-molecular N-H?O and N-H?N hydrogen bonds occur, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C-H?O hydrogen bonds link the mol-ecules into inversion dimers with R 2 2(14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C-H?? and ?-?-stacking inter-actions [centroid-to-centroid distances = 3.631?(2) and 3.631?(2)?Å], forming a three-dimensional network. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from H?H (39.3%), C?H/H?C (18.0%), O?H/H?O (15.6) and S?H/H?S (10.2%) inter-actions.

| S-EPMC6775743 | biostudies-literature

The crystal structure, Hirshfeld surface analysis and energy frameworks of 2-[2-(meth-oxy-carbon-yl)-3,6-bis-(meth-oxy-meth-oxy)phen-yl]acetic acid.

Project description:In the title compound, C14H18O8, (I), the meth-oxy-carbonyl [-C(=O)OCH3] and the acetic acid [-CH2C(=O)OH] groups are inclined to the benzene ring by 79.24?(11) and 76.71?(13)°, respectively, and are normal to each other with a dihedral angle of 90.00?(13)°. In the crystal, mol-ecules are linked by a pair of O-H?O hydrogen bonds forming the familiar acetic acid inversion dimer. The dimers are linked by two C-H?O hydrogen bonds and an offset ?-? inter-action [inter-centroid distance = 3.6405?(14)?Å], forming layers lying parallel to the (10) plane. The layers are linked by a third C-H?O hydrogen bond and a C-H?? inter-action to form a supra-molecular framework.

| S-EPMC7336770 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of <i>N</i>-[(2-hy-droxy-naphthalen-1-yl)(3-methyl-phen-yl)meth-yl]acetamide.

Project description:The title compound, C20H19NO2, is of inter-est as a precursor to biologically active substituted quinolines and related compounds. This compound crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angles between mean planes of the methyl-phenyl ring and the naphthalene ring system are 78.32?(6) and 84.70?(6)° in mol-ecules A and B, respectively. In the crystal, the anti-ferroelectric packing of mol-ecules A and B is of an ABBAABB type along the b-axis direction. The crystal structure features N-H?O, O-H?O and weak C-H?O hydrogen bonds, which link the mol-ecules into infinite chains propagating along the b-axis direction.

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Crystal structure and Hirshfeld surface analysis and energy frameworks of 1-(2,4-di-methyl-phen-yl)-4-(4-meth-oxy-phen-yl)naphthalene.

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| S-EPMC6038635 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 4-(4-chloro-phen-yl)-5-methyl-3-{4-[(2-methyl-phen-yl)meth-oxy]phen-yl}-1,2-oxazole.

Project description:In the title compound, C24H20ClNO2, the mean planes of 4-chloro-phenyl, 2-methyl-phenyl and phenyl-ene rings make dihedral angles of 62.8 (2), 65.1 (3) and 15.1 (2)°, respectively, with the 5-methyl-1,2-oxazole ring. In the crystal, mol-ecules are linked by inter-molecular C-H⋯N, C-H⋯Cl, C-H⋯π contacts and π-π stacking inter-actions between the phenyl-ene groups. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (48.7%), H⋯C/C⋯H (22.2%), Cl⋯H/H⋯Cl (8.8%), H⋯O/O⋯H (8.2%) and H⋯N/N⋯H (5.1%) inter-actions.

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The crystal structure and Hirshfeld surface analysis of 1-(2,5-di-meth-oxy-phen-yl)-2,2,6,6-tetra-methyl-piperidine.

Project description:In the title compound, C17H27NO2, the piperidine ring has a chair conformation and is positioned normal to the benzene ring. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, forming chains propagating along the c-axis direction.

| S-EPMC7274006 | biostudies-literature

2-[(4-Chloro-phen-yl)sulfan-yl]-2-meth-oxy-1-phenyl-ethan-1-one: crystal structure and Hirshfeld surface analysis.

Project description:The title compound, C15H13ClO2S, comprises (4-chloro-phen-yl)sulfanyl, benzaldehyde and meth-oxy residues linked at a chiral methine-C atom (the crystal is racemic). A twist in the methine-C-C(carbon-yl) bond [O-C-C-O torsion angle = 19.3?(7)°] leads to a dihedral angle of 22.2?(5)° between the benzaldehyde and methine+meth-oxy residues. The chloro-benzene ring is folded to lie over the O atoms, with the dihedral angle between the benzene rings being 42.9?(2)°. In the crystal, the carbonyl-O atom accepts two C-H?O inter-actions with methyl- and methine-C-H atoms being the donors. The result is an helical supra-molecular chain aligned along the c axis; chains pack with no directional inter-actions between them. An analysis of the Hirshfeld surface points to the important contributions of weak H?H and C?C contacts to the mol-ecular packing.

| S-EPMC5947492 | biostudies-literature

Crystal structure, Hirshfeld surface analysis, inter-action energy and DFT studies of 4-[(4-allyl-2-meth-oxy-phen-oxy)meth-yl]-1-(4-meth-oxy-phen-yl)-1<i>H</i>-1,2,3-triazole.

Project description:In the title mol-ecule, C20H21N3O3, the allyl substituent is rotated out of the plane of its attached phenyl ring [torsion angle 100.66 (15)°]. In the crystal, C-HMthphn⋯OMthphn (Mthphn = meth-oxy-phen-yl) hydrogen bonds lead to the formation of (100) layers that are connected into a three-dimensional network by C-H⋯π(ring) inter-actions, together with π-π stacking inter-actions [centroid-to-centroid distance = 3.7318 (10) Å] between parallel phenyl rings. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (48.7%) and H⋯C/C⋯H (23.3%) inter-actions. Computational chemistry reveals that the C-HMthphn⋯OMthphn hydrogen bond energy is 47.1 kJ mol-1. The theoretical structure, optimized by density functional theory (DFT) at the B3LYP/ 6-311 G(d,p) level, is compared with the experimentally determined mol-ecular structure. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC7273996 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of 1,3-bis-[2-meth-oxy-4-(prop-2-en-1-yl)phen-oxy]propane.

Project description:The asymmetric unit of the title compound, C23H28O4, comprises two half-mol-ecules, with the other half of each mol-ecule being completed by the application of twofold rotation symmetry. The two completed mol-ecules both have a V-shaped appearance but differ in their conformations. In the crystal, each independent mol-ecule forms chains extending parallel to the b axis with its symmetry-related counterparts through C-H⋯π(ring) inter-actions. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (65.4%), H⋯C/C⋯H (21.8%) and H⋯O/O⋯H (12.3%) inter-actions. Optimized structures using density functional theory (DFT) at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structures in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC7057369 | biostudies-literature

12-(3,4,5-Tri-meth-oxy-phen-yl)-2,3,4,12-tetra-hydro-1H-5-oxa-tetra-phen-1-one: crystal structure and Hirshfeld surface analysis.

Project description:In the title compound, C26H24O5, the pyran ring has a flattened-boat con-formation, with the 1,4-related ether O and methine C atoms lying 0.1205 (18) and 0.271 (2) Å, respectively, above the least-squares plane involving the doubly bonded C atoms (r.m.s deviation = 0.0208 Å). An envelope conformation is found for the cyclo-hexene ring, with the flap atom being the middle methyl-ene C atom, lying 0.616 (2) Å out of the plane defined by the remaining atoms (r.m.s. deviation = 0.0173 Å). The fused four-ring system is approximately planar, with the dihedral angle between the least-squares planes through the cyclo-hexene and naphthyl rings being 10.78 (7)°. The tris-ubstituted benzene ring occupies a position almost perpendicular to the pyran ring [dihedral angle = 83.97 (4)°]. The most prominent feature of the packing is the formation of zigzag supra-molecular chains mediated by aryl-C-H⋯O(meth-oxy) inter-actions; chains are connected into a three-dimensional architecture by methyl-ene- and methyl-C-H⋯π inter-actions. The prevalence of C-H⋯O and C-H⋯π inter-actions is confirmed by an analysis of the Hirshfeld surface. A comparison with related structures suggests that the mol-ecular conformation of the title compound is relatively robust with respect to varying substitution patterns at the methine C atom of the pyran ring.

| S-EPMC4908558 | biostudies-literature

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